Enantioselective Synthesis of Functionalized β-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids

被引：11

作者：

Mondal, Santigopal ^{[1
,3
]}

Mukherjee, Subrata ^{[1
,3
]}

Das, Tamal Kanti ^{[1
,3
]}

Gonnade, Rajesh G. ^{[2
]}

Biju, Akkattu T. ^{[1
,3
,4
]}

机构：

[1] CSIR NCL, Organ Chem Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] CSIR NCL, Ctr Mat Characterizat, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[3] Acad Sci & Innovat Res AcSIR, New Delhi 110020, India

[4] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 17期

关键词：

N-HETEROCYCLIC CARBENES; DYNAMIC KINETIC RESOLUTION; PROMOTED BIS-CYCLIZATIONS; ASYMMETRIC-SYNTHESIS; ACYL AZOLIUMS; KETO ACIDS; TRANSFORMATIONS; ORGANOCATALYSIS; CYCLOADDITION; CYCLOPENTENES;

D O I：

10.1021/acs.joc.7b01526

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Heterocyclic carbene (NHC)-catalyzed intramolecular aldol lactonization of readily available ketoacids leading to the enantioselective synthesis of cyclopentane-fused beta-lactones is presented. The reaction proceeds via the generation of NHC-bound enolate intermediates formed from the ketoacids in the presence of the peptide coupling reagent HATU and NHC generated from the chiral triazolium salt. The functionalized beta-lactones are formed under mild conditions in high yields and enantioselectivities.

引用

页码：9223 / 9228

页数：6

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